Alpha-hydroxy-ether of fatty acid soap



Patented Feb. 10, 1948 ACID soar Herbert H. Guest, West Hartford, Conn, asslgnor to The J. B. Williams Company. Glastonbury, Conn, a corporation of Connecticut No Drawing.- Application November 13, 1944, Y

Serial No. 583,312

This invention relates to new chemical compounds or soaps, which are suitable for use as, detergents and wetting agents, and to new. and.

improved shaving and cosmetic preparations incorporating the new chemical compounds. More particularly, this invention is directed to the soaps of the novel iii-substituted higher fattyacids described in my copending application. Ser. No. 556,083, of which the present application is a contlnuation-in-part, and to new and improved shavi'ng creams, shaving soaps and cosmetic preparations incorporating these compounds.

In my copending application I have described and claimed certain novel alkanol-ether acids comprising saturated higher fatty acids of the Cu to Cu group containing an aliphatic substituent having at least one hydroxyl in the alphaposition to the carboxyl group of the acid. Suchz acids may be prepared by reacting an a-halo higher fatty acid or an ester or salt thereof, with an alkali metal derivative of a pqlyhydric alcohol such as a glycol or glycerol, and acidifying the re- 15 (oi. zoo-4'13) the alkali metal, and alkanolamine salts thereof,

.possess very valuable properties as a result oftheir high solubility in water. Those of the Cu and Cu acids are especially desirable, since they are readily soluble even in sea water or hard waters of a high degree of hardness. They are rapid foam producing, and form a latherwhich holds much more water than the lather of soaps made by saponifying coconut acids. They also possess the much sought property of being mild orbland in feeling when applied to the face or skin. They have improved emollient and hairsoftening properties, and do not dry on the skin,

as do the soaps of the coconut group (Palmae) now generally used. Moreover' my new soaps are soluble enough not to form jelly-like soaps. They are especially valuable for use in shaving creams, shaving soaps, and cosmetic preparations requiring a, softening or emulsifying agent, since they sulting reaction mixture. In this way there are j I prepared new chemical compounds which are acids of the C1: to Cu group, more particularly those acids having an even number of carbon atoms such as lauric acid, myristic acid, palmitic acid and stearic acid. containing in the alpha position to the carboxyl group the residue from the polyhydric alcohol attached through the oxygen] atom of one of its hydroxyls.

Typical new chemical compounds prepared in accordance with the process disclosed-in my co-- pending application include a(2,3-propan'edioll-ether) octadecanoic acid (also called a-glyceryl stearic acid) a-(z-ethanol-l-eth'er) octadecanoic -a-haloge'n acidsof their salts or esters, as undes- 5 acid (also called a-ethylene glvcol-steari acid) c-(propane-Z-ol-ether) octadecanoic acid (9.186"

dodecanoic acid (lauric acid); tetradecanoic acid (myristic acid) and hexadecanoic acid (pal'mitic acid). The polyhydrlc alcoholiwhose alkali metal derivative is reacted with the a-halo higher fatty conditions, it is ordinarily unnecessary-in the prepara'tion of other soaps to first prepare the acid and then neutralize it with the base to form acid or its salt or ester maybe a glycolor substituted glycol, such as ethylene glycol or propylene glycol; glycerol; or a polyhydriq alcohol wherein the hydroxyl groups are not on adjacent carbon atoms, or not on terminaLcarbon atoms, such as 2-methyl-2,4-pentanediol.

I have found th t the snaps of the acids disdo not possess the skin-irritant effects characteristic of the coco soaps formed from the lower molecular weight fatty acids which make up the bulk of the coconut oils used in preparing the usual commercial toilet soaps and shaving creams or soaps.

In preparing the improved soaps to which this invention is directed, I may proceed with the preparation of the lit-substituted acids as disclosed in my co-pending application, and, after separation of the acid, neutralize the same with the base selected."thereby producing the desired soap. While this method is especially useful for preparingthe alkanolamine soaps, since-it is not possible to prepare them by the process described in, my co-pending application starting with the sired amino compounds are formed under these the soap. By following theprocess describedand claimed in my copending application. omitting the final acidification step, but removing the salt formed as, one of the products ofreaction, it is possible to prepare soaps of sufllcient purity to permit their incorporation in such preparations":

as shaving soaps and creams without the acces sity of first going through the stage in which the r-substituted acid is prepared in relatively l-pure'form. 1

Accordingly, in" preparing suchcompounds as the alkali metal soaps oi the novel c-subs uted acids described in my copending application,

whether those soaps be common alkali metal closed in my cop ding applicationfparticularly' ll soaps, such as sodium orpotassium soaps, or the acidifying the reaction mixture to produce the acid, the resulting paste or jelly may be treated to remove the salt formed as one of the prodnets of the reaction. This may be done by simply allowing the salt to settle out, or it may be expedited by dissolving the soap in alcohol, flltering to remove the salt, and then driving off the alcohol by distillation. The purified soap may then be incorporated with or mixed with other ingredients usual in toilet soaps, shaving creams, shaving soaps. or those cosmetic preparations which contain wetting or emulsifying agents.

In some cases where a very pure soap is wanted it is desirable first to prepare the free d-$1lb$tituted acid having the residue of the polyhydric alcohol in the alpha position to the carboxyl group, and then react the alkali metal or amine base therewith; Generally in preparing the alkanolamine soaps this method is util'zed as in this way it is possible to avoid the undesired side reaction wherein undesired amino compounds are formed.

As examples 01' my process for producing the new soaps of very soluble and free lathering characteristics, greater emollient and hair-softening pr per ies, and a mild or bland feeling on the skin, the following may be given as illustrative:

EXAMPLE 1 Soars or a-GLYCERYL Srsmuc Acm Glycerol in the amount of 200 grams was dehydrated by d stilling it with 100 grams of xylene,

' first at atmospheric pressure, and then under reduced pressure, until all the water and hydrocarbon were removed, including a small amount of glycerol. At the same time sodium ethylate was prepared by dissolving 5 grams of sodium in 100 grams of absolute ethanol. This solution was added to the anhydrous glycerol, and ethanol distilled oil. There was thus obtained a solution of sodium glycerinate in glycerol.

. glycerinate to form sodium a-glyceryl stearate,

methanol, and sodium bromide.

The resulting paste comprising the sodium soap of a-glyceryl stearate, also termed the sodium soap of (it-(2,3, propanediol-l-ether) octadecanoic acid, could be used as such for some toilet soaps, shaving creams, shaving soaps, cosmetic preparations or similar preparations if the impurity present therein is not objectionable. Preferably, it is first freed from sodium bromide either by settling, or by dissolving in ethanol, filtering to remove the metal salt, and then distilling oil the alcohol to yield a relatively pure soap.

If soaps of other bases are desired, the unpurified reaction mixture may be acidified to secure the tit-substituted acid, in accordance with the The pure acid may be recovered, and'thcn neutralized by the addition of any base to form the corresponding soap. Thus, caustic soda could be used in the neutralization to form a sodium soap; potassium hydroxide to form a potassium soap, or an alkanolamine such as mono, di, or triethanolamlne to form the corresponding alkylol amine soaps.

EXAMPLE 2 Soars or a-ETHYLENI Gmrcor. s-rmssrc Am A sodium derivative of glycol was prepared by adding 4.7 grams of metallic sodium to 280 grams of substantially anhydrous ethylene glycol, To this solution there was then added 25 grams of the methyl ester of a-chlorostearic acid. The mixture was heated to the reflux temperature and refluxed for approximately one hour. a

The resulting'reaction mixture was filtered to separate the precipitated sodium chloride, and then distilled under a reduced'pressure less than atmospheric to remove excess glycol. The resulting pasty product was the sodium soap of a-ethylene glycol stearic acid, also termed a-(2-ethanol-l-ether) octadecanoic acid. It may be incorporated in shaving creams and soaps, toilet soaps, and cosmetic preparations.

Should it be desired to prepare substantially pure soaps oi. other bases, the substantially pure acid may first be prepared by acidifying the reaction mixture and separated as disclosed in my copending application. This substantially pure acid may then be neutralized by the addition or any alkali metal base, or alkanola'mine base. to form the corresponding soaps oi the a-substituted fatty acid.

EXAMPLE 3 Soars or a-PROPYLENI: Garcon Srnssrc Acrn The sodium derivative of propylene glycol was prepared by adding 6.5 grams or metallic sodium in small amounts to 210 grams of propylene glycol; The solution was then added to 50 grains of e-bromostearlc acid dissolved in 50 grams of benzene, The reactants were stirred and the reaction was complete in one-half hour, the temperature not exceeding 100 ,0. Excess glycol was then removed by distillation of the reaction mixture under a pressure less than atmospheric.

The pasty material was essentially the sodium soap o1 a-propylene glycol, which may be also named the sodium soap of a-(propane-2-ol-lether) octadecanoic acid. It could be used without purification in some shaving and cosmetic.

preparations, or in toilet soaps, but is advantageously freed of sodium bromide by dissolving in ethanol and filtering. By distilling ofl the alcohol the substantially pure soap is obtained.

Instead of purifying it to free it of sodium bromide the reaction product might be converted to the corresponding acid by acidification as described in my copending application. The substantially pure acid may then be separated, and neutralized, or substantially neutralized, with any alkali metal base, or alkanolamine base, to form,

the corresponding soaps oi the a-substituted fatty acid in substantially pure form.

. A PLE 4 Soars or a-GLYCIIRYL Psrmrro Acrn distilling it with 100 grams of xylene, first at atprocess described in my copending application. mospheric pressure, and then at reduced pres- The resulting potassium soap or a-propylene' glycol myristic acid, also termed a-ipropanez This was;

ethanol distilled off, thereby resulting in a solu-, I

tion of sodium glycerinate in glycerol.

Fifty grams of a-bromopalmiticacid were added to the sodium glycerinate. and the mixture heated to 100 C. for one-half hour. at the end of which time thereaction was complete. The resulting product. comprising the sodium salt of a-glyceryl palmitic acid, also termed a-(2,3-propanedioi-l-ether) hexadecanoic acid, maybe used as such in some toilet soaps or shaving or cosmetic preparations. However, it is preferable to first free it from sodium bromide by dissolving in ethanol, filtering, and distilling of! the alcohol.

If soaps other than the sodium soap are de sired, or if an extremely pure sodium soap should be needed for any special purpose, the reaction mixture may be converted to the corresponding (ii-substituted acid, as described in my appending application, and this acid then neutralized or sub tantially neutralized. -with the particular alkali metal base or alkanolamin'e base whose'soap is desired. v l.

' E AM Boers or a-PaorxmmsGnvcor. Mvxrsrrc Acrn Sodium soap-.

Seven grams of metallic sodium were dissolved in a mixtureof 100 grams of-absolute ethanol and 100 grams of propylene glycol. Excess alcohol was distilled off and distillation continued until a small amount (10 grams) of the glycol had also --'jf been distilled over. The distillation was first car-- ried out at atmospheric pressure, and then under reduced pressure in a partial vacuum.

After thesolu'tion of the sodium derivative of propylene glycol thus produced had cooled, it was added to aflask containing 40 grams of methyl a-bromomyristate. The resultingreaction mixture was heated for half an hour at 100 C. until the reaction was complete.

The resulting sodiumsoap of a-propylene glycol myristic acid, also termed a-(propane-z-ol-lether) tetradecanoic acid, could be utilized without purification in certain shaving and cosmetic preparations and in toilet soaps; "However it is preferably first freed of sodium bromide by dissolving in ethanol and filtering. Aiter distilling oil the alcohol it is secured in a pure state.

If soaps other thanthe sodium soap are desired, the acidmay be prepared by acidification as described inlmy depending applicationfand this acid then-neutralized or substantially neutralized by the base corresponding'to-the soap desired. This base may be ,an alkali metal base, such as sodium hydroxide, potassium hydroxide or lithium hydroxide, or an ethanolamine base.

Potassium soap Propylene glycol in the :amount of grams was added to a-solution of 15 grams of solid potassium hydrate (KOH-l 'in 100 grams of absolute alcohol, and the mixture distilled, first at atmospheric pressure, and then under reduced pressure less than atmospheric, until grams of the mixed alcohol and glycol had been distilled off from the mixture.

The resulting potassium derivative of propylene glycol was mixed with 30 grams of methyl a-bromomyristate andthe mixture heated at 100 C. for one-halfjhour.

ol-l-ether) tetr'adecanoic acid, maybe utilized as such, or it might be freed of potassium bromide EXAMPLEB Soars or a-Gnvcaaxr. S'rnnro Acrp Solid potassium hydroxide pellets in the amount of 15 grams were dissolved in 100grams of absolute ethanol by heating under a reflux condenser. Glycerol in the amount oi 150 grams,

which had'previously been heated to 210 C. for a short time in order to render it substantially anhydrous, was then added. to the alcohol solution.

The resulting mixture was then distilled, first at atmospheric pressure and then under partial y vacuum until glycerolbegan to appear inthe distillate.

The resulting potassium glycerinate solutionwas then cooled and mixed,.with-mechanlcal stirring, with 30 grams of methyl a-bromostearate. The resulting mixture was heated to C. for one-half hour.

The resulting reaction mixture containing the potassium soap of a-glyceryl stearic acid, also termed a-(2,3 propanediol-l-ether) octadecanoic acid, could be utilized directly in some toilet and shaving preparations. It is first preferably freed of potassium bromide by dissolving in ethanol, filtering, and evaporation of the alcohol to give the pure soap.

I'f soaps other than the potash soap are desired, the sub tantially. pure acid may be prepared by acidification of the reaction mixture in accordance with the method disclosed in my copending application, and this acid neutralized with a base to produce the desired soap. Any of the previously specified bases may be utilized, or, if alkaline earth metal soaps should be desired for any reason (although not utilizable as soluble soaps), the bases of the alkaline earth metals, such as calcium hydroxide and barium hydroxide, may be used to effect the neutraliza- Fifteen grams of solid potassium'hydroxide were dissolved in 50 grams of absolute ethanol by heating. To the resulting solution 100 grams of propylene glycol were added, andthe mixture distilled. first at atmospheric pressure, and then at a pressure less than atmospheric. Distillation was continued until 70 grams of unreacted ethanol and glycolwere distilled over.

The resulting solution of the potassium derivative of propylene glycol was cooled and then added to 25 grams ofmethyl a-chlorolaurate with mechanical stirring. The resulting reaction mixture was heated to" C. for 25 minutes until reaction was complete.

The resulting potassium soap of a-propylene glycol lauric acid. also termed a-(propane-2-ol-1- ether) dodecanoic acid, is preferably freed o2 potassium chloride by dissolving in ethanol, filtering, and distilling off the alcohol. This gives the pure soap for incorporation in shaving creams or soaps, or in cosmetic preparations.

Should soaps other than the potash soap be desired, the reaction mixture may be converted to the free acid by acidification in accordance with the method of my copending application, and the resulting, substantially pure, free acid neutralized, or substantially neutralized, with any of the bases previously referred to to produce the desired soaps.

EXAMPLE 8 Soars or oz-( 1,3 Dmrm-3-HYnaoxY-1-Errmn Burma) -Ocrsnncanoro Acrn Anhydrous ethanol in the amount of 100 grams was reacted with five grams of metallic sodium. After all the sodium had dissolved. 110 grams of 2-methyl-2,4 pentanediol were added, and the mixture subjected to distillation, first at atmospheric pressure, and then under reduced pressure less than atmospheric. The distillation was continued until approximately 103 grams of unreacted ethanol and alcohol were distilled over. This resulted in a solution of the sodium derivative of 2-methyl-2,4-pentanediol. v

This solution was then added to 30 grams of a-bromostearic acid and the, reaction mixture heated for one hour at 100 C. The resulting sodium soap of fl-(1,3 dimethyl-3-hydroxy-1- ether butane) -octadecanoic acid when then freed of sodium bromide by dissolving in ehtanol, filtering, and distilling oil the alcohol. This gives the pure soap for incorporation in shaving creams, shaving soaps, cosmetic preparations, toilet soap, etc.

However, if substantially pure soaps of other bases are desired, the free acid may be prepared by acidification of the unpurified reaction mixture, in accordance with the process of my copending application, and this acid neutralized with any alkali, or with an ethanolamine base to produce the desired soaps in the substantially pure state.

EXAMPLE 9 ALKANOLAMINE SOAPS or a-GLYCERYL Srmiuc ACID Fifty grams of e-glyceryl stearic acid, also called iZ'(2,3 propanediol-l-ether) octadecanolc acid, prepared as described in my copending application, were melted and mixed with 10 grams of monoethanolamine. This is an excess of the amine of 25% over the theoretical amount. The mixture was stirred to secure complete homogenization. The resulting thick paste was the monoethanolamine soap of a-glyceryl stearic acid. It was readily soluble in water and had good detergent qualities. While it does not foam readily, the soap is a good emulsifying agent.

For identification purposes the soap was heated to 130-150" C. for one hour. It was converted into an amide that was insoluble in water, but was readily soluble in, and could be recrystalized from, ethanol. The amide melted at 113 C. and had the formula:

In a similar manner other amine soaps can be prepared from anyof. the other a-substituted higher fatty acids described and claimed in my copending application. While I have taken the monoethanolamine soap as illustrative, similar soaps can, of course, be prepared by using other alkanolamines such as diethanolamlne or triethanolamlne. While the soaps may vary somewhat. in their lathering properties, all are good emulsifying agents.

EXAMPLE 10 Sonrom Soar or or-GLYCERYL SrnAaIc A011) grams of absolute ethyl alcohol was reacted with 7 grams of metallic sodium, the metal being'added gradually to the alcohol. When all of the sodium had dissolved, 100 grams of dehydrated glycerin (100%) was added. The mix. ture was then distilled in order to completely remove the ethanol. To the residue. which consisted of sodium glycerinate and glycerin. there was added 35 grams oi a-chloromethylstearate. The mixture was then heated for one hour at a temperature of -170" C.

In order to free the resulting soap from sodium chloride, the reaction mixture was dissolved in ethanol, filtered, and the alcohol then distilled off. The soap could then be used in the preparation of shaving soaps, toilet soaps, and similar preparations.

- A typical formula for shaving cream, utilizin" the sodium soap of a-glyceryl stearic acid, also called the sodium soap of d-(2,3 propanediol-lether) octadecanoic acid, as thus prepared, may be as follows:

All percentages are by weight, based on the totak weight of the shaving cream.

In place of the glycerin, any glycol could be utilized to produce similar soaps which might be employed in the shaving cream formula in place of the sodium soap of a-glyceryl stearic acid.-

Thus, soaps could be prepared by utilizing propylene glycol. diethylene glycol. ethylene glycol or 2-methyl-2,4 pentanedioi in place of the glycerin.

EXAMPLE 11 POTASSIUM Soar or a-GLYCERYL SrzAnrc Am 25 grams of solid potassium hydroxide was dissolved in 100 grams of absolute ethanol. Dehydrated glycerol in the amount of 100 grams was added, and the ethanol completely removed by distillation.

After cooling, there was added 75 grams of methyl a-bromostearate. The resulting mixture was heated cautiously, with stirring. After onehalf hour of heating at 150 C. the reaction was complete.

Ethanol was added to the reaction mixture to dissolve the potassium soap of e-glyceryl stearic acid present therein, and the resulting solution filtered to free it from potassium bromide. The alcohol was then removed by distillation. The resulting substantially pure soap could be used for shaving and cosmetic preparations, or in the manufacture of commercial toilet soaps.

EXAMPLE 12 Pornssmu Soar or a-Paorrrrm: GLYCOL Lmarc Acm I potassium hydroxide was 15 grams of solid The resulting potash soap of a-propylene glycol.

lauric acid was a pasty product, very soluble in water.

EXAMPLE 13' Soars or a-PROPYLENE GLYCOL Mvaxsrrc Acm A mixture of 100 grams of absolute ethanol and 100 grams of propylene glycol was reacted with '7 grams of metallic sodium. After the sodium had completely dissolved, the ethanol was removed by distillation.

There was then added 40 grams of methyl abromomyristate gradually, with stirring. The reaction mixture was heated at 100 C. for about one-half hour.

The resulting sodium soap of a-propylene glycol myristic acid could be used as formed, or

it could be further purified by acidifying the reaction mixture with dilute mineral acid, as. for example, with 10% sulfuric acid. This resulted in an oil which was washed and dried on the steam bath. Its analytical values agreed with those calculated for CH3.(CH2)11.CH(OCH2.CHOH.CH3) .COOH

An amine soap of this acid was prepared by adding the calculated amount of triethanolamine necessary to neutralize the acid. The amine soap thus resulting formed a clear jelly at room temperature. It was soluble in hard water and in sea water, as well as in oil and in organic liquids such as benzene.

The sodium salt in very pure form was prepared by neutralizing the acid with the calculated amount of sodium hydroxide. This soap was a paste that :was soluble in water, but not in oils. It foams freely even in salt water.

EXAMPLE l 4 Amna Soars or a-GL'YCERYL PALMITIC Acm 20 grams of a-glyceryl palmitic acid, prepared in accordance with the process described in my copending application, was neutralized with the calculated amount (6 grams) of 2-amino-2- methyl-1,3-propanediol. There resulted a soft paste, very soluble in water, which possessed excellent wetting properties? The product was the alkanolamine soap of a-glyceryl palmitic acid, and was of considerable value when incorporated in shaving creams and soaps.

EXAMPLE Soars or a-GLYCERYL Srnaarc AcIn The alcohol was distilled out 10 The soap was used in making up a shaving cream having the following formula:

Parts Potassium soap of a-glyceryl stearic acid..---- 30 Stearic acid 30 P0 t a s s i u m hydroxide solution (specific gravity 1.5) Water All parts are by weight.

The percentage of soap in the shaving cream may be varied within considerable limits to impart any desired degree of foaming to the cream. The potassium soap could also be replaced, either wholly or in part, by theamine soap of a-glyceryl stearic acid, prepared by a process similar to that described in Example 13. The properties of the shaving cream are considerably improved by incorporating up to five parts of the amine soap as part of the total thirty parts of soap. as the wetting effect on the beard is thereby considerably improved.

The soaps prepared in accordance with my invention, including the alkali metal and alkanolamine soaps of the acids described in m ccpending application, are characterized by certain remarkable properties not found in the soaps of the coconut group (Palmae), which are at present universally used in making commercial soap-containing preparations. In addition, they have the important advantage that they can be prepared from starting materials which are readily available in this country, and which do not have to be imported.

My new soaps yield a free or copious lather in all kinds of water, including the hard waters common to large areas of the United .States. They do not have the skin-irritant effects characteristic of the soaps prepared from the lower molecular weight acids making up the bulk of the coconut oils. They are mild or bland in feeling on the face, and have greater emollient and hairsoftening properties, since they do not tend to dry as readily as the coconut soaps.

As typical examples of my new soaps I may refer to the sodium soaps of a propylene glycol myristic acid and iii-propylene glycol iauric acid. They are very soluble in water, lathering readily,

possessing good detergent action even in sea water.

Among other typical soaps the sodium or tassium soaps of a-glyceryl stearic acid are remarkable for their solubility in water. even water of a high degree of hardness, as contrasted, for

example, with sodium stearate which is almost insoluble in cold water.

The alkali metal soaps prepared in accordance with my invention can be readily salted out of solution with sodium hydroxide or sodium chloride. Alkaline earth metal soaps, such as the barium soaps, are readily formed by adding an alkaline earth metal salt, such as a solution of barium chloride, to a solution 01' the alkali metal soap. The alkaline; earth metal-soap precipitates out as a solid, which is generally white in color.

My new soluble soaps, constituting the alkali metal, and alkanolamine salts of the iii-substituted higher fatty acids described and claimed in my copending application, may be represented generically bythe formula:

R.CH,OY

where R is an alkyl radical containing at least 10 carbon atoms;'Y a polyhydric alcohol residue;

and M an alkali metal or alkanolamine residue. Since I am particularly concerned with the a-substituted acids having an even number of carbon atoms of the saturated series extending from Iauricacid to stearic acid, R is preferably an alkyl radical selected from the group which consists of decyl, dodecyl, tetradecyl. and hexadecyl.

Since the iii-substituted higher fatty acid is Joined through an ether linkage with the polyhydric alcohol residue substituent in the alpha position, my new soaps may also be represented by the following generic formula: v

s acuocno M where R is an alkyl radical containing at least carbon atoms; S is a radical selected from the group which consists of hydrogen and alkyl radicals; Q is a substituted aliphatic group containing at least one, hydroxyl substituent; and M denotes a salt-forming radical, such as an alkali metal, an alkaline earth metal, or an alkanolamine residue. For water-soluble soaps M may represent an alkali metal, or an alkanolamine residue. 7

My invention is particularly applicable to preparing mixed soaps of a-substituted palmitic and stearic acids having the polyhydric alcohol residue attached in the alpha position to the carboxyl group. such as result when derivatives of the stearic acid of commerce is employed in preparing the soaps. The stearic acid of commerce is a mixture iof palmitic and stearic acid, and the mixture ofsoaps resulting is utilizable for any purpose in preparing shaving creams, shaving soaps, cosmetic preparations, toilet soaps, or

, other compositions requiring a highly soluble soap product possessing good detergent properties, exactly as if it were a pure product instead of a mixture.

'Ilhe foregoing description and exam les are intended merely to be illustrative of certain preferred embodiments of my invention. Modifications thereof which conform to the spirit of the invention, or variations therefrom, as they may be within the scope of the appended claims, are to be considered as part of my invention.

I claim:

1. A water-soluble soap of an (it-substituted higher fatty acid having the formula:

higher fatty acid having the formula:

R. CH.OCH1.CH:OH

COOM

where R is an alkyl radical having an even number, from ten to sixteen inclusive, of carbon atoms; and M is an alkali metal.

3. A water-soluble soap of and-substituted higher fatty acid having the formula:

R.CH.OCH2.CHOH.CE|OH COOM where R is 'analkyl radical having an even number, from ten to sixteen inclusive, of carbon atoms: and M is an alkali metal.

4. Sodium a-(2,3 propanediol-l-ether) octadecanoicate.

5. Sodium a-(2-ethanol-l-ether) octadeoanoicate.

6. The method of producing a water-soluble alkali metal soap of an tit-substituted higher fatty acid which comprises reacting an alkali metal derivative of a simple functional, saturated, aliphatic, polyhydric alcohol having less than four hydroxyl groups with a compound selected from the group which consists of, the saturated cr-hfllO- gen substituted higher fatty acids having twelve to eighteen carbon atoms, and their salts and esters,

7. The method of producing a soluble alkali metal soap of an iii-substituted higher fatty acid, which comprises reacting an alkali metal derivative of a simple functional, saturated, aliphatic, polyhydric alcohol having less than seven carbon atoms and less than four hydroxyl groups with a saturated a-halogen substituted higher fatty acid having twelve to eighteen carbon atoms.

8. A water-soluble soap of an iii-substituted higher fatty acid having the formula:

R.CH.OY

where R is an alkyl radical containing at least ten carbon atoms; and Y is a simple functional, saturated, aliphatic, polyhydric alcohol residue, said resldue'containing less than seven carbon atoms and less than three hydroxyl groups, and M is an alkali metal.

9. A water-soluble soap of an lit-substituted higher fatty acid having the formula:

R.CH.OY

where R is an alkyl radical containing at least ten carbon atoms; and Y is a simple functional saturated, aliphatic, polyhydrio alcohol residue, said residue containing less than four carbon atoms and less than three hydroxyl groups, and M is an alkali metal.

10. A lather-forming preparation adapted for shaving which includes, as a lather-forming constituent thereof, a water-soluble soap of a 41-811)- stltuted higher fatty acid having the formula:

R.CH.OY

OOH

where R is an alkyl radical containing at least ten carbon atoms, and Y is a simple functional, saturated, aliphatic, polyhydric alcohol residue, said residue containing less than three hydroxyl groups.

11. A lather-forming preparation adapted for shaving which includes, as a lather-forming constituent thereof, a water-soluble alkali metal soap of,an lit-substituted higher fatty acid having the formula:

R.CH.OY

OOH

where R is an alkyl radical containing at least ten carbon atoms, and Y is a simple functional, saturated, aliphatic, polyhydric alcohol residue, said residue containing less than four carbon atoms and less than three hydroxyl groups.

12. A lather-forming preparation adapted for shaving which includes, as a lather-forming constituent thereof, a water-soluble alkanolamine aesasss l3 soap of an tit-substituted hisher fatty acid havinl the formula: I

. aomov R.CH.OY

OOH

where R is an alkyl radical containing at least ten carbon atoms, and Y is a simple functional, saturated, aliphatic, polyhydric alcohol residue, said residue containing less than four carbon atoms and less than three hydroxl groups; with substantially stoichiometric amounts of an alkanolamlne.

14. A water-soluble soap of an a-substltuted higher fatty acid having the formula;

where R is an alkyl radical containing at least ten carbon atoms; and Y is a simple functional, saturated, aliphatic, polyhydric alcohol residue,

14 said residue containing less than seven carbon atoms and less than three hydroxyl maps, and M is an alkalolamine.

15. A water-soluble soap of an a-substituted higher fatty acid having the formula:

ILCILOY where R. is an alkyl radical containing at least ten carbon atoms; and Y is a simple functional,

saturated, aliphatic. polyhydric alcohol residue, said residue containing less than iourcarbon atoms and less than three hydroxyl groups, and M is an alkalolamine.

HERBERT H. GUEST.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES Pam'rs Number Name Date 2,109,929 Risby Mar. 1, 1938 2,277,015 Guest Mar. 17, 1942 2,277,016 Guest Mar. 17, 1942 OTHER REFERENCES Low and Harrow, "An introduction to Organic Chemistry," ed. 5, 1940, John Wiley 8; Sons. N. Y.

Karrer, Organic chemistry," N. Y. 1938. 

